diff --git a/nucypher/cli/commands/alice.py b/nucypher/cli/commands/alice.py
index d3f81f58b..5861542ac 100644
--- a/nucypher/cli/commands/alice.py
+++ b/nucypher/cli/commands/alice.py
@@ -330,7 +330,7 @@ def config(general_config, config_file, full_config_options):
     emitter = setup_emitter(general_config)
     if not config_file:
         config_file = select_config_file(emitter=emitter,
-                                         checksum_address=full_config_options.pay_with,
+                                         checksum_address=full_config_options.config_options.pay_with,
                                          config_class=AliceConfiguration)
     updates = full_config_options.get_updates()
     get_or_update_configuration(emitter=emitter,
diff --git a/nucypher/cli/commands/bob.py b/nucypher/cli/commands/bob.py
index f35bb684e..0d1d87ec1 100644
--- a/nucypher/cli/commands/bob.py
+++ b/nucypher/cli/commands/bob.py
@@ -73,7 +73,7 @@ class BobConfigOptions:
 
         self.provider_uri = provider_uri
         self.signer_uri = signer_uri
-        self.gas_strategy = gas_strategy,
+        self.gas_strategy = gas_strategy
         self.domains = {network} if network else None
         self.registry_filepath = registry_filepath
         self.checksum_address = checksum_address
@@ -116,6 +116,7 @@ class BobConfigOptions:
         checksum_address = self.checksum_address
         if not checksum_address and not self.federated_only:
             checksum_address = select_client_account(emitter=emitter,
+                                                     signer_uri=self.signer_uri,
                                                      provider_uri=self.provider_uri)  # TODO: See #1888
 
         return BobConfiguration.generate(
diff --git a/nucypher/cli/commands/ursula.py b/nucypher/cli/commands/ursula.py
index 2e57d7f86..daf01c8dd 100644
--- a/nucypher/cli/commands/ursula.py
+++ b/nucypher/cli/commands/ursula.py
@@ -174,13 +174,17 @@ class UrsulaConfigOptions:
 
     def generate_config(self, emitter, config_root, force):
 
-        assert not self.dev  # TODO: Raise instead
+        if self.dev:
+            raise RuntimeError('Persistent configurations cannot be created in development mode.')
 
         worker_address = self.worker_address
         if (not worker_address) and not self.federated_only:
             if not worker_address:
                 prompt = "Select worker account"
-                worker_address = select_client_account(emitter=emitter, prompt=prompt, provider_uri=self.provider_uri, signer_uri=self.signer_uri)
+                worker_address = select_client_account(emitter=emitter,
+                                                       prompt=prompt,
+                                                       provider_uri=self.provider_uri,
+                                                       signer_uri=self.signer_uri)
 
         rest_host = self.rest_host
         if not rest_host:
@@ -258,8 +262,11 @@ class UrsulaCharacterOptions:
 
     def create_character(self, emitter, config_file, json_ipc, load_seednodes=True):
 
+        # TODO: embed compatibility layer?
         ursula_config = self.config_options.create_config(emitter, config_file)
         is_clef = ClefSigner.is_valid_clef_uri(self.config_options.signer_uri)
+
+        # TODO: Oh
         client_password = None
         if not ursula_config.federated_only:
             if not self.config_options.dev and not json_ipc and not is_clef:
diff --git a/nucypher/cli/utils.py b/nucypher/cli/utils.py
index 94375714f..8770b27f2 100644
--- a/nucypher/cli/utils.py
+++ b/nucypher/cli/utils.py
@@ -88,13 +88,9 @@ def make_cli_character(character_config,
     #
 
     # Produce Character
-    try:
-        CHARACTER = character_config(known_nodes=teacher_nodes,
-                                     network_middleware=character_config.network_middleware,
-                                     **config_args)
-    except (CryptoError, ValueError):
-        raise character_config.keyring.AuthenticationFailed(f"Failed to unlock nucypher keyring. "
-                                                            "Are you sure you provided the correct password?")
+    CHARACTER = character_config(known_nodes=teacher_nodes,
+                                 network_middleware=character_config.network_middleware,
+                                 **config_args)
 
     #
     # Post-Init